Market overview
Allowed, with material limits. New licenses are limited: the cap is full.
Key West issues no new residential transient licenses, so rentals of less than 28 days are legal only at a property that already holds a city transient license and medallion.
Property eligibility: Not assessed A market overview can't tell whether a specific home qualifies (zoning, permits, HOA).
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Stays of 28 nights or more fall outside the short-term rental rules, but come under their own lease rules.
Guests staying this long can gain tenant rights, such as protection from eviction.
Not legal advice. The legal framework, notes and sources are in the full report.
17 rules on record for Key West, 9 of them from government sources. Every rule traced to its official source. How we research
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Source: City of Key West Permit and Licensing Business Center (cityofkeywest-fl.gov, official), checked 5 Nov 2026. Official links, citations and how to apply come with a paid plan.
Yes, with material limits. Key West issues no new residential transient licenses, so rentals of less than 28 days are legal only at a property that already holds a city transient license and medallion.
Yes, a license or registration is required.
12.5% in total on stays, on our records.
No night cap is on record.
Fines of up to $500 are on record.
Stays of 28 nights or more fall outside the short-term rental rules, but come under their own lease rules. Guests staying this long can gain tenant rights, such as protection from eviction.
We last checked the short-term rental rules for Key West on 5 Nov 2026.
LawfulStay tracks short-term rental rules for 5,120+ places, with every rule traced to its official source.
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